There were already whispers that Troy Aikman could land some type of role with the Dallas Cowboys, given his ESPN contract is set to expire after Super Bowl LXI and there’s no extension in place just yet.

And as the Cowboys faced the Philadelphia Eagles in Week 7 on Monday Night Football, Aikman and Jerry Jones were caught on camera having a lengthy conversation on the sideline, which only fuelled the rumors of a potential role for Aikman in the front office.

However, longtime Cowboys insider Ed Werder isn’t convinced the sideline conversation means Aikman is on the verge of joining the Dallas brass.

Troy Aikman’s Past With Jerry Jones Could Stand in the Way

Jones selected Aikman with the first overall pick in the 1989 NFL Draft, and the two went on to be part of one of the most successful stretches in franchise history. The Cowboys won Super Bowls XXVII, XXVIII, and XXX during Aikman’s 12 seasons, claiming three titles in a four-year span in the 1990s.

They haven’t won another Super Bowl since.

Aikman retired after the 2000 season and hasn’t held a formal role with the organization yet. Throughout Aikman’s playing career, Jones served as both the Cowboys’ owner and general manager.

Aikman addressed their relationship publicly last week, describing it as complicated but built on respect. He also said he would be open to sitting down with Jones, whether or not a job was on the table.

Then, Dallas Morning News beat reporter Joseph Hoyt posted a video on X showing Aikman and Jones in what appeared to be a lengthy sideline conversation. Werder, a longtime Cowboys insider, retweeted the clip with his take on the interaction and why a professional reunion could be difficult.

“Troy played for GM Jerry. He didn’t think it went all that well. I don’t see him working in the Cowboys’ front office, regardless of what happens on TV,” Werder wrote.

Werder’s point was that the version of Jones who controlled every football decision during Aikman’s career is the same person who would be Aikman’s boss if he joined the front office now, and that history will influence the picture regardless of how much mutual respect exists between them.

Meanwhile, on the gridiron, the Cowboys beat the Eagles 38-21, pulling away in the fourth quarter after Philadelphia failed to convert on a fourth down deep in their own territory. Javonte Williams ran 25 times for 155 yards and a touchdown, the first time a Cowboys back had gone for 150 or more yards since Ezekiel Elliott in 2018.

Dak Prescott threw three touchdowns, while CeeDee Lamb caught five passes for 74 yards and two scores.

Through Week 7, Prescott ranks No. 10 in the league with a PFN QB Impact Score of 80.2. He has thrown for 1,851 yards and 13 touchdowns against five interceptions while completing 65.2% of his passes this year.

Philadelphia, now without Jalen Hurts for the rest of the season, fell to 2-5 after losing to rival Dallas, marking its fifth consecutive defeat.

The NFC East remains more open than expected at this point in the season. The Giants sit at 4-2-1, with the 3-4 Cowboys 1½ games back.

The Commanders have also struggled with Jayden Daniels dealing with injuries, leaving Dallas with a visible path to the division title.